


People You Meet in New York

by Adaquinn



Category: Iron Man (Movies), Supernatural
Genre: Multi
Language: English
Status: In-Progress
Published: 2012-09-16
Updated: 2012-09-16
Packaged: 2017-11-14 09:40:57
Rating: Mature
Warnings: Graphic Depictions Of Violence
Chapters: 2
Words: 4,082
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/513878
Author URL: https://archiveofourown.org/users/Adaquinn/pseuds/Adaquinn
Summary: <blockquote class="userstuff">
              <p>Dean comes to New York, chasing a demon, leading him to a chance encounter with Pepper Potts and Tony Stark.  His boundaries get a little widened.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

  * For [whiteraven1606](https://archiveofourown.org/users/whiteraven1606/gifts).



> Written for WhiteRaven1606. Lead up to naughtiness.

Dean hated hunting in a big city. They didn’t get much bigger than New York. The bastard demon was running down a dark alley. Dean chasing him quickly. People were in the alley, of course. Dean swore creatively as he tried to keep the knife hidden.   
The demon burst out onto a street heading for another alley. Before he slid into the darkness he grabbed a civilian. The professionally dressed red head gasping as she’s pulled into the alley. Dean put on a burst of speed as he heard her scream. Instead of fear it sounded more like anger. He ran into the alley. The red head was kicking firmly. Her hands reaching back to beat on him. Dean smirked a little, wouldn’t do her a bit of fucking good, but she had balls. He lifted the knife, the demon pulled the redhead directly in front of him.  
“Now now. We don’t need to hurt the pretty thing do we?” The demon asked. He sniffed over the woman’s shoulder. The redhead turned to look at him. She kicked his shin hard. The demon just grinned at her.”  
“You’ve picked the wrong woman.” She said. Her elbow came back hard against his stomach. The demon grunted and loosened his hold on her slightly. She pulled out a small flashlight device. She pointed it at him and pushed the button.  
A flash of light repelled the demon away from her. He hit the back of the wall with a thud. He growled and took a step towards her, murder gleaming in his eyes. He blinked and revealed the black on black eyes. The woman yelped and stepped back. Dean grabbed the back of her jacket. He pulled her behind him and threw the knife.   
The knife landed in his chest with a thud. The demons eyes widened before the lightening started under his skin. He fell forward slumping to the ground. Dean panted and turned to look at the woman. Her eyes were wide and bright blue. She looked at him.  
“Oh… Oh dear.” She panted softly. Dean let her go and went to the body, he kicked it over and pulled the knife out. He wiped it off on the demon’s clothes.  
“What kind of fucking flashlight is that?” Dean asked her.   
“It’s… it’s a repulsor.” She said, shaking. Dean stood up, he held the knife lightly.  
“Okay, we need to get out of here.” He said, putting a hand on her shoulder. He heard a sound above him. He looked up, gripping her shoulder and pushed her away from him.  
“TONY!” The redhead yelled. “Don’t!”  
Dean saw a flash of light and then felt himself get pushed back against the wall. He slumped to the ground. His last thought -When did demons start flying?-  
\-------------------------------------------------------------------  
Dean woke up slowly, hearing voices talking around him. His eyes slowly opened and he saw the redhead settle in beside him. She handed him a bag of frozen peas.

“You okay?” He asked as he tried to sit up on the couch. He put the peas against the back of his head. The woman smiled warmly.  
“She’s fine. Sorry about the attack. I see a guy standing next to her with a knife I get a little reactive.” A man’s voice said. Dean turned to see a man sitting on the counter. He wore jeans and a t-shirt. Something glowing under the shirt on his chest.  
“Fair enough.” Dean said. He blinked trying to clear his head.  
“Thank you for helping me.” The woman said. She put a soft hand on his shoulder. “I’m Pepper. This is Tony.” She waved her hand towards the other man.  
“Dean.” He said, offering a hand to the man who came to shake it. Dean looked around. The apartment he was in looked very posh. He felt a little out of his element. He looked back to Pepper.  
“Well, it was sort of my fault he snatched you in the first place. I hate chasing things through a city. Way too many casualties waiting to happen. I’m glad you’re okay.” Dean gave her a wide flirtatious smile. Pepper’s cheeks flushed slightly. Tony grinned and lifted an eyebrow. He shook his head slightly. Pepper turned to look at him, she gave him a wink.  
“Thanks anyway. Although the killing part may have been a little overboard.” Tony said, he sipped a bottle of water. Dean glared at him.  
“Listen, you don’t understand. There was no reasoning with it. No slap on the wrist was going to stop that bastard. The only way to stop a demon is to kill a demon. Send his ass right back to hell.”  
Tony lifted an eyebrow and looked to Pepper. She shrugged her shoulders lightly.  
“Demon huh?” He said dryly. He stood up and walked in front of Dean, he sat on the arm of a chair. “Maybe you hit that wall a little harder than I thought.”  
Dean pressed his lips together, his eyes narrowed slightly. He stood up and tossed the frozen peas to Tony.  
“Don’t treat me like a three pound bag o’ crazy.” He growled. “You don’t know shit about what’s out there.” Dean pointed out of the window, her jaw clenched.  
Tony looked up at him calmly. A little sarcastic smile on his lips. Dean glowered at him. He always considered himself the king of the smart-ass smile. Now he realized how utterly annoying it was. Glad to know it was effective.  
“I’ll show myself out.” Dean said as he turned for the door.  
“Dean it’s okay.” Pepper glared at Tony who lifted his shoulder slightly. She put her hand on Dean’s shoulder.  
“I know that whatever it was, it wasn’t human.” She said soothingly. She looked to Tony. “His eyes turned black. It was like sharks eyes. Have you ever heard of anything like that?” Tony frowned and stood up.  
“Jarvis, any of that sound familiar to you?” He asked.  
“Yes Sir.” Jarvis answered. Both Tony and Dean looked up surprised.   
“Where the HELL am I?” Dean asked.   
“Stark Towers.” Pepper answered softly.  
“What do you mean “Yes Sir”? Jarvis, there is no such thing as demons.” Tony complained.   
“Stark Towers?” Dean parroted her. He looked to Tony and then to Pepper. “Wait, does that mean…” He asked. Pepper smiled to him.  
“Yes I’m Tony Stark.” Tony answered. He moved to the interface with Jarvis.  
“There is several books on the matter of Demonology. There are proven accounts.”  
“Why haven’t I heard of it?” Tony demanded.  
“It wasn’t in Popular Mechanics, Sir.”  
“Or Maxim.” Pepper supplied helpfully. Tony gave her a look and she smiled sweetly to him. Her hands still on Dean’s arm. Tony sighed and went to the bar.  
“I need a drink.”


	2. The Deed is done

**Summary for the Chapter:**

> Man on Man fluff. With some assistance from Pepper.

He’d been a guest for a few days. Pepper was worried that the knock on Dean’s head was serious. He’d had a lot worse in his travels. For some reason he had difficulty telling Pepper no. Dean took another drink of the beer Tony offered him. The rich had much better alcohol than they served in the roadhouses he typically visited. He leaned against the bar, his eyes half closed. He glanced up, looking at the couple in the kitchen. Pepper was smiling up at Tony. Dean smirked a little, he knew that smile. It was the one that no man could say no too. He shook his head slightly, wondering what she was asking.

“Pepper, I don’t think he swings that way.” Tony said, looking at their guest. Dean was dressed in jeans with a black shirt and a flannel over it. He had to admit, the man was handsome. He looked back down to Pepper who smiled wider.

“Have I ever been wrong?” She asked with a soft chuckle. She leaned in, brushing her lips against Tony’s neck. He felt his heartbeat quicken. He ran his hand down her back. 

“Okay, so Clint was sort of a surprise.” He admitted. He shifted a little and she smiled wider. Her fingers trailed over his chest. She smiled and winked to him. She turned and headed towards the bedroom. Tony dragged his hands over his hair and sighed. He looked back to Dean who was giving him a smirk. He stood and grabbed another beer. Alcohol was going to be needed. He went to the bar. “So, you’re going to stay for another few days?” Tony asked.

Dean shook his head and watched Tony pour two tumblers of whiskey. “I should be heading back. Sam is gonna get himself in trouble I leave him alone to long. He does stupid when I’m not there.”

Tony looked at Dean for a moment. It was hard to think of Dean as the one who’d be the level headed of the two. He seemed to be a little reckless and wild. Of course Tony was known to hide his feelings behind bravo and bullshit.

“So, what is Pepper trying to talk you into?” Dean asked. Tony laughed and pushed the beer towards him. He gave a broad smile to Dean.

“New York is demon free?” He asked. Dean tilted his head slightly. It was a rather sloppy cover up, maybe it was something embarrassing.

“Probably not. There’s a lot of vice and hardship in this town. But no way I can search the whole city. The one I wanted is dead.” He knocked on the chrome of the bar. “So, I have to ask. Stark has always put out fantastic weapons. I never had my hands on one. But I know they can saw through just about anything. Why did you stop making them?”

Tony frowned slightly. He took a drink of his whiskey. His eyes stayed low. He was trying to figure out how to answer that.

“I get it.” Dean said. Tony looked up at him, his brows coming together. Dean smiled, his eyes revealing that he really did get it. Tony shifted slightly, the bullshit part of his mind wasn’t giving him anything. “You got tired of supplying the darkness of the world.” Tony’s stomach twisted slightly. His version of darkness and Dean’s were only different on the surface. Dean smiled a little wider. He took the bottle of the whiskey. He refilled Tony’s glass and his own.

Tony chuckled softly and made his way around the bar. He leaned next to Dean and picked up his glass. He stood just close enough to feel how Dean’s body warmed the air. Dean glanced over to him, his brows drawing in slightly. He looked at the whiskey and then drank it down.

“Dean, that’s forty year scotch.” Tony said dryly.  
“Damn good forty year old scotch.” Dean said with a grin. He looked over Tony’s shoulder. His eyebrows came up sharply. His jaw slacked slightly. Tony turned around and saw Pepper in one of his white shirts. It came down just enough to see the tops of her thigh highs. She smiled and came towards them. Tony grabbed the bottle of whiskey and filled Dean’s glass again.  
“You’re going to want to drink that.” He murmured.  
“Dude, do I need to leave?” Dean murmured back. Tony laughed and shook his head. He leaned back on the bar and watched Pepper stride up to him. She rolled to her tiptoes and kissed his cheek. The hem of the shirt lifting up just enough to reveal her black silk panties. She smiled to Dean, who looked rather shocked.

Tony moved to the couch, carrying the scotch with him. He chuckled softly as Pepper slid her hand into Dean’s. It was always fun to see Pepper shed her sweet efficient persona. Revealing the naughty voyeur underneath. It always took everyone by surprise. She tugged lightly towards the couch. Dean looked at her. He drank down the scotch and meekly followed her.

She settled him next to Tony. Dean looked at him, his hazel eyes wide. Tony just nodded and took the glass away from him. 

“Uh. Is this gonna get freaky?” He asked. Pepper smiled brightly and nodded. Tony just chuckled. Pepper crawled into Dean’s lap. She leaned against him kissing him. Dean felt a jolt of lust dance up his spine. She tasted sweet. His hands rested on her thighs. His hands slid up the silken legs. His fingers dragged over her skin. His pants started to feel tight. Pepper purred and rocked her hips against him.

Dean growled and slide one hand up to cup her neck. He kissed her firmly. His fingers slid under the shirt. He cupped her ass with one hand and held her closer. She pushed his flannel down his arms. Dean leaned closer to her, pulling his arms away from her to get the shirt off. 

Tony carefully stood up as to not remind Dean that he was here yet. He reached back pulling his shirt off. He threw it where Pepper tossed Dean’s flannel. He came closer, pulling Peppers hair away from her neck. He leaned down, kissing the pale column of her neck. Pepper shivered, her fingers drawing over Dean’s arms. Dean slid his hand up the back of Pepper’s shirt. His hands flattening over her skin. Pepper groaned loudly, feeling Tony behind her and Dean under her. She tugged up Dean’s t-shirt. Dean growled against her lips.

Tony lightly bit Pepper’s neck, his hands sliding over her arms. His fingers lightly brushed over Dean’s ribs. His fingers moving over Dean’s skin with Pepper’s hands. Dean went still for a moment.

“Uhm. Is this something where Tony likes to watch?” Dean asked, feeling other hands move on him. Pepper shushed him lightly and kissed him again. Dean’s shirt was pulled off. He looked over Pepper’s shoulder and saw Tony there. Dean blinked once and Tony just gave him a broad smart-assed smile. Dean chuckled slightly nervous. He shrugged slightly and went back to kissing Pepper.

Pepper drug her fingers over Dean’s chest. His shoulders were broad, she could feel the strength of his muscled torso. She groaned softly and rocked towards him. Tony bit her neck lightly again. His hands slid down over Dean’s stomach. His fingers felt the soft hair that lead down to Dean’s cock. Pepper started to kiss Dean’s jaw. He tilted his head back, groaning as her lips glided over his skin. He felt himself harden under her. It pressed uncomfortably against his zipper. His hands gripped her thighs, then he pressed his hands up until he felt the silk of her panties.

Tony looked up seeing Dean’s eyes closed. Pepper was kissing down to his shoulder. Tony wrapped his arm around Pepper’s waist. He lightly pulled her back. His hand slide over Dean’s jean encased cock. He bit his lip feeling the hardness. He eased his hand up to the buttons. He swiftly opened Dean’s fly. The stiff column pushed up out of his jeans. Dean groaned with pleasure. Tony leaned closer, he gently kissed Dean’s lips. 

Dean’s eyes popped open wide. Tony went still. His lips barely touching Dean’s. Dean panted quickly. Tony’s eyes holding his. Tony leaned forward more. His lips grazing over Dean’s. Tony’s tongue lapped Dean’s lower lip. Dean shuddered deeply. Pepper eased to sit on Dean’s left leg. Her fingers glided down his chest and wrapped around his cock. Dean gasped and Tony kissed him. His tongue rubbing against the other man’s. Dean’s heart pounded hard. Pepper’s gentle fingers moving over his turgid length. 

“Fuck,” Dean murmured against Tony’s mouth. Tony just chuckled and moved closer to Dean. His hands slid down, wrapping with Pepper’s around Dean.

“That is the idea.” Tony joked softly.

Dean’s hips jerked forward as he felt a second hand join. His eyes fluttered hard. Pepper leaned forward, kissing his neck, down his shoulder. Her fingers kept moving with Tony’s. Her blood running hot. She loved stroking someone with Tony. She let her lips drag up, teasing Dean’s ear as he kissed Tony. 

Dean was being gently overwhelmed with sensations. His cock throbbed as Pepper and Tony stroked him. His hand was still on Pepper’s thigh. Dean wasn’t sure what to do with his other one. Tony had moved closer to him with Pepper sitting on Dean’s leg. Dean’s hand hovered slightly, he wasn’t sure where to touch Tony. He put his hand lightly on Tony’s hip. The other man groaned against his lips. Dean’s fingers slide up, feeling the muscled side of Tony’s ribs. It was very different from what Dean was used too. It wasn’t unpleasant. He felt the “What the hell am I doing?” thought rising in the back of his mind. Pepper nibbled on his earlobe and the thought went silent.

Pepper eased off of Dean’s lap. Her fingers still stroking him. Tony shifted closer to him. His other hand slid up, lightly caressing Dean’s side. Dean groaned and kissed Tony a little harder. Pepper gently eased her lips off of Dean’s ear. She watched Dean for a moment, making sure he wasn’t going to freak out. He seemed to be enjoying himself. His hand left her thigh. It slid up Tony’s arm, lightly catching him by the neck. Pepper groaned seeing Dean’s strong hands cup Tony’s neck. She’d always loved watching Tony with men.

Tony growled against Dean’s lips. He felt Dean’s fingers capture the nape of his neck. He returned the kiss hotly. His fingers moving up and down Dean’s column. His thumb dragged over the tip. He felt Dean shiver, his cock leaking precum. Pepper stood up and came up behind Tony. She wrapped her arms around him and opened up his pants. She kissed his shoulder and pushed down his jeans. Her fingers stroking his length. Tony was already hard and shaking. 

She stepped back and took a seat on the coffee table. Tony stepped back and held Dean’s arm. He brought him up to stand by the couch. Dean pushed his jeans down. He stepped out of them and Tony did the same. Pepper bit her lip. Dean was nearly the same height as Tony. Their chests were pressing together. Deans hand slid down Tony’s back. Their cocks lightly rubbed together. Tony’s hand stretched, wrapping around both shafts. He rocked his hips, the precum from both of them making his cock glide against Dean’s. Dean panted, his hips rocking forward. His hand slid down and gripped Tony’s ass. He moaned as they rocked together, slipping and sliding in Tony’s hand. 

“Fuck that feels good.” Dean groaned. Tony smiled and brushed his lips over his. Their cocks grinding as they fucked his hand. Tony’s other hand glided up Dean’s back. He turned so his back was to the couch, Dean facing him. Dean’s hands gripped Tony’s ass, his hips thrusting, pushing his cock into the tight grip of Tony’s hand. Dean panted, his head falling back. Tony kisses his throat and left small bite marks along his collar bone. Dean dragged his nails over the curve of Tony’s ass. His body shuddered hard. He felt Tony’s ass clench. Dean looked down. His hand gently moving Tony’s to the side. He looked down, watching the two thick crowns push in and out of Tony’s hand. He felt his sac tighten. Electricity zipping up his back. Tony stepped back, pulling his cock away from Dean’s. Dean made a strangled growl. His eyes opened. His fingers tightened on Tony’s neck. Tony chuckled and sat down on the couch. Dean looked up at the ceiling, trying to figure out what to do. He felt himself on the edge of cumming.

Tony leaned forward and wrapped his mouth around Dean’s crown. Dean shuddered, his knees going weak for a moment. He held himself up with Tony’s shoulder. Tony’s hands reached up, grabbing Dean’s hips.

“Jesus fucking Christ!” Dean gasped as Tony’s mouth sucked him. Dean’s fingers gripped the back of Tony’s neck. His ass clenched as he pushed his hips forward. Tony’s lips slide up his column until they wrapped around the base of Dean’s cock. Tony’s throat clenching around Dean’s cock. Dean’s head fell back, he shook as he found the rhythm Tony mouth.   
“Fuuucckkk” Dean growled. He panted and dragged his fingers through Tony’s short hair.

Pepper bit her lip, her eyes wide as she watched her lover go down on Dean. Her thighs pressed hard together as the heat built between her legs.   
“Jarvis.” She whispered softly.  
“Yes, I’m recording” Jarvis said softly through the speaker closest to her.   
“Good boy.” She murmured.

She stood up. She pulled a condom out from her pocket. She came up behind Dean. She kissed his shoulders as she opened the small package. She lightly ran her fingers over Tony’s. Feeling Dean’s skin beneath their touch. Dean growled softly as Tony pulled his mouth back. He leaned back against the couch, grinning up at Dean. Tony stroked his cock, watching as Pepper wrapped Dean’s. She stroked him as she put it on. She got lube from the table and made Dean’s cock slippery. Dean leaned against her, he could feel his heart beat throb through his cock. 

He knelt down and leaned forward. He brushed a kiss over Tony’s chest. He kissed up to his neck and then kissed his mouth. He dragged the tip of his cock against opening of Tony’s ass. Tony’s breath caught. He groaned, pushing back, his hand gripping Dean’s shoulder as his ass stretched to take Dean’s tip. His nails marked Dean’s shoulder. 

Dean gently pushed forward. He felt Tony clench around him. Dean panted softly and growled as he felt Tony’s nails. He tilted his head back. Pepper was behind him stroking his chest, watching his cock sink slowly deeper into Tony. She purred softly in Dean’s ear. Her hand reached forward and wrapped around Tony’s cock. Tony’s hips jerked, he gasped heavily. Pepper and Dean smiled. Dean pushed until the curve of Tony’s ass settled against his thighs. He went still for a moment. His eyes watching as Pepper stroked Tony.

“Dean, don’t you dare stop.” Tony growled out. His fingers tightened on Dean’s shoulder. Dean gave a strangled chuckle. His fingers rubbed over Tony’s chest. He lightly pinched Tony’s nipples. Tony groaned and pressed harder against Dean. 

“Not sure I could.” Dean said. He slowly pulled back, until only the tip of his cock was still in Tony. Pepper’s hand caressed up Dean’s back, her other hand stroking Tony’s column. Tony twisted on the couch, his lashes fluttering lightly.

Dean pushed forward, gently easing himself back into Tony. He found a nice slow pace, feeling his sac throb as Tony’s ass clenched him. Dean leaned forward, his strong body leaning over Tony’s. He pressed a kiss to Tony’s neck. Pepper’s hand moved down Dean’s arm. She guided his hand to Tony’s cock. Her fingers twining with his. Both of them gliding up and down Tony’s length. His sac started to pulse slightly. Tony twisted on the couch. Hungrily pushing back against Dean. His back arched and he growled.

Dean felt Tony flutter around him. His hand tightened on Tony’s cock. He cried out pounding his hips against Tony’s ass. His head fell back as he cried out. The orgasm shot through his body. It throbbed with ever spurt of Dean’s cock. Tony shuddered, feeling Dean throb inside him. His cock pulsed as cum spilled over Pepper and Dean’s hands. His hips jerked and another fount of seed spilled. Tony felt his ass milk Dean’s cock.

Dean panted as he melted over Tony’s body. His hands moving over Tony’s slide. His length still buried in Tony. Pepper eased her hand from between them. She sat on the couch, she smiled. Dean pressed his face against Tony’s neck. His heart beating hard against his chest. He could feel Tony’s cock pressed against his stomach.

He lifted his head and looked at Tony and Pepper. Pepper grinned and gave him a wink. Dean flushed brightly. He leaned back. His hands wrapping around the base of his length, holding the condom as he pulled out. He swallowed, looking at the cum covering his hand, on his stomach and covering Tony’s stomach.

Tony relaxed against the couch, waiting for his breathing to return to normal. He groaned as Dean eased out of him. He grabbed his t-shirt. He quickly wiped up himself and Dean. He took Dean’s hand and stood up. 

“Think about it tomorrow.” Tony said. He walked to the bedroom, bringing Dean with him. Pepper grinned and followed along.


End file.
